Tyler's Takes: 'When Harry Met Sally' is the Perfect Rom-Com

Romantic comedies are cheesy and have, over time, given a narrative that follows the same formulaic beats: Boy meets girl, they fall in love, have their ups and downs, the conflict separates them, they get back together in the climax, and live happily ever after. In 1989, however, When Harry Met Sally took this formula and breathed new life into the subgenre with a different plot structure and charm that hadn’t been seen in a rom-com, not before nor after. It’s surprising that a defining film such as this hasn’t been endlessly copied, although I’d suspect no one wants to take up the challenge of comparison. When Harry Met Sally distinguishes itself through sharp writing, genuine character development, and a realistic portrayal of relationships that resonates with viewers across generations. For over 30 years, it has been hailed as perfect and, in my opinion, considered the quintessential romantic comedy. 

One of the reasons When Harry Met Sally stands out is its deeply relatable characters. Harry and Sally are not caricatures or idealized versions of romantic leads—they are flawed, complex, and deeply human. Harry is cynical about relationships, believing that men and women cannot be friends because sex will always get in the way. On the other hand, Sally is optimistic but neurotic, with particular habits that are both endearing and frustrating. The film captures the authenticity of their evolving relationship, from their initial animosity to their eventual friendship and finally to love. Unlike many romantic comedies that rush characters into relationships, When Harry Met Sally allows time for Harry and Sally to grow as individuals. Their relationship develops organically for years, and the audience sees the highs and lows of their connection, making their eventual romance feel earned and believable.

The film also depicts how relationships aren’t linear. Life happens—timing is often imperfect, and emotions are complicated. When Harry and Sally finally realize their love for one another, it’s not a big moment but rather the beginning of a relationship that will require effort and compromise. This sense of realism contributes to the movie's timeless appeal, while Ephron’s sharp script comments on relationships and insightful observations about love and friendship while balancing humor. The conversations between Harry and Sally are simultaneously funny and profound, exploring topics that range from the trivialities of dating to the deeper complexities of loneliness and emotional vulnerability. On the other hand, the film has several funny moments that compliment the film’s spirit. Yes, there are laugh-out-loud moments like Sally’s orgasm scene, but there are also subtle humorous moments, such as Harry and Jess talking about Harry’s divorce while doing the wave at a football game. 

The chemistry between Crystal and Ryan is undeniably key to the film’s success. Both actors bring their characters to life in a way that feels authentic and grounded. Crystal’s portrayal of Harry’s cynicism is balanced by moments of warmth and vulnerability. In contrast, Ryan’s neuroses and optimism for Sally make her a character you can’t help but root for. One of the most memorable aspects of the film is Ryan’s performance in the Katz’s Delicatessen scene, where Sally fakes an orgasm in front of a packed restaurant to prove a point about men’s ability to recognize genuine female pleasure. Moreover, both Crystal and Ryan expertly handle the transition from friendship to romance, making the shift feel natural and earned. Their performances are understated yet powerful, adding depth to what could have been a more superficial romantic storyline in lesser hands.

When Harry Met Sally is as much about timing as it is about romance. The film spans over a decade, chronicling the different stages of Harry and Sally’s lives, from their initial meeting after college, their respective relationships with other people, and their eventual romantic connection. Ephron’s script also makes a case that When Harry Met Sally showcases something rom-coms have consistently failed at: honesty. The exploration of timing is crucial to the film’s honest commentary and emotional resonance. It shows that love doesn’t always happen when we expect or want it to. Sometimes, two people can be perfect for each other, but the timing is off. Harry and Sally’s journey reminds the audience that love is often messy and complicated and requires emotional growth and maturity.

At its core, When Harry Met Sally is a film about the blurred lines between love and friendship. The central question of the film—whether men and women can indeed be friends without romantic feelings getting in the way—is one that resonates with audiences of all ages. The film’s exploration of friendship as a precursor to romance also sets it apart from many other rom-coms. While many films in the genre rely on “love at first sight” or grand romantic gestures, When Harry Met Sally takes a more nuanced approach, showing that sometimes the best relationships are the ones that develop over time, built on a foundation of mutual respect, trust, and understanding. The film’s themes of loneliness, heartbreak, and the fear of commitment are universally relatable. Harry and Sally’s struggles with finding love and navigating relationships reflect the experiences of many viewers, making the film feel personal and universal.

When Harry Met Sally is the perfect romantic comedy because it transcends the limitations of the genre and showcases how rom-coms can and should be done. It captures the complexities of love and friendship in a way that resonates with audiences of all ages, making it a film that continues to be beloved more than 30 years after its release. In a world of predictable rom-coms, When Harry Met Sally remains the shining example of what the genre can achieve. No one in the movie, not even Reiner and his two leads, could predict how stronghearted this movie could be and that it remains untouched after all this time. By the time the credits roll, it makes any romantic or cynic pause for a moment and says to themselves, “I’ll have what they’re having.”

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